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H0500

Sigma-Aldrich

1,2,3,4-Tetrahydroharmane-3-carboxylic acid

Synonym(s):

1-Methyl-1,2,3,4-Tetrahydropyrido[3,4-b]indole-3-carboxylic acid, 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, NSC 26225

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About This Item

Empirical Formula (Hill Notation):
C13H14N2O2
CAS Number:
5470-37-1
Molecular Weight:
230.26
MDL number:
MFCD00022199
UNSPSC Code:
12352100
PubChem Substance ID:
24895402
NACRES:
NA.22

storage temp.

−20°C

SMILES string

CC1NC(Cc2c1[nH]c3ccccc23)C(O)=O

InChI

1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)

InChI key

ZUPHXNBLQCSEIA-UHFFFAOYSA-N

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Application

Reactant involved in synthesis of molecules for biological studies including:
  • Cytotoxicity and insecticidal activities of harmine derivatives
  • Isoquinolines, β-carbolines, and 3-deazapurines via oxidative decarboxylation
  • Cytotoxic evaluation of 1,3-di- and 1,3,9-trisubstituted β-carbolines

Biochem/physiol Actions

Implicated in eosinophilia-myalgia syndrome associated with L-tryptophan ingestion.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Formation and determination of aldehyde-addition products of tryptophan.
K Meyer et al.
Advances in experimental medicine and biology, 398, 711-717 (1996-01-01)
J G Zangrilli et al.
Biochemistry and molecular biology international, 37(5), 925-933 (1995-11-01)
Eosinophilia-myalgia syndrome (EMS), a recently described inflammatory disorder characterized by myalgia, peripheral eosinophilia, and multisystem inflammation is associated with L-tryptophan consumption. Fibrosis of various tissues due to excessive accumulation of type I collagen is a prominent late manifestation of the
From the Centers for Disease Control. Analysis of L-tryptophan for the etiology of eosinophilia-myalgia syndrome.
JAMA, 264(13), 1656-1656 (1990-10-03)
D E Brenneman et al.
The Journal of pharmacology and experimental therapeutics, 266(2), 1029-1035 (1993-08-01)
The L-tryptophan eosinophilia myalgia syndrome (L-TRP-EMS), an inflammatory syndrome characterized by eosinophilia, myalgias, perimyositis, fasciitis and neuropathies, occurred in epidemic proportions in the United States in the summer and fall of 1989. The neuropathic clinical features in L-TRP EMS are
Y Ogawa et al.
Archives of toxicology, 67(4), 290-293 (1993-01-01)
1-Methyl-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) may cause eosinophilia-myalgia syndrome (EMS) associated with ingestion of L-tryptophan. The distribution and excretion of MTCA were studied in rats which had received perorally a single 1.6 mg/kg dose of MTCA. MTCA concentrations in blood, kidney, liver
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